ethyl 6-ethoxymethylenecyclohex-2-enecarboxylate

Base Information

• Chemical Name: ethyl 6-ethoxymethylenecyclohex-2-enecarboxylate
• CAS No.: 79236-14-9
• Molecular Formula: C₁₂H₁₈O₃
• Molecular Weight: 210.273
• Mol file: 79236-14-9.mol

Synonyms:

Chemical Property of ethyl 6-ethoxymethylenecyclohex-2-enecarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 6-ethoxymethylenecyclohex-2-enecarboxylate

There total 2 articles about ethyl 6-ethoxymethylenecyclohex-2-enecarboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

ethyl 6-formylcyclohex-2-enecarboxylate (4567-31-1) + orthoformic acid triethyl ester (122-51-0) → ethyl 6-ethoxymethylenecyclohex-2-enecarboxylate (79236-14-9)

Guidance literature:

With toluene-4-sulfonic acid; 1.) room temperature, 24 h, 2.) 150-160 deg C, 2 h;

DOI:10.1039/P19810001557

Reference yield:

ethyl (2E)-penta-2,4-dienoate (13369-23-8) → ethyl 6-ethoxymethylenecyclohex-2-enecarboxylate (79236-14-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 76 percent / 12 h / 90 - 95 °C

2: 100 percent / toluene-p-sulphonic acid / 1.) room temperature, 24 h, 2.) 150-160 deg C, 2 h

With toluene-4-sulfonic acid;

DOI:10.1039/P19810001557

Reference yield:

ethyl 6-ethoxymethylenecyclohex-2-enecarboxylate (79236-14-9) → methyl 6-formyl-6-methylcyclohex-1-enecarboxylate (79236-18-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / zinc-copper couple, iodine / diethyl ether / 1 h / Heating

2: 1.) conc. hydrochloric acid, 2.) aq. potassium hydroxide / 1.) ethanol, reflux, 2.5 h, 2) reflux, 4 h

With hydrogenchloride; potassium hydroxide; zinc copper; iodine; In diethyl ether;

DOI:10.1039/P19810001557

upstream raw materials:

ethyl 6-formylcyclohex-2-enecarboxylate

orthoformic acid triethyl ester

ethyl (2E)-penta-2,4-dienoate

Downstream raw materials:

methyl 6-formyl-6-methylcyclohex-1-enecarboxylate

ethyl 6-formyl-6-methylcyclohex-2-enecarboxylate

methyl 6-formyl-6-methylcyclohex-2-enecarboxylate

Refernces

• 1、 Tokoroyama, Takashi,Fukuyama, Yoshiyasu,Kubota, Takashi,Yokotani, Kenji. "Synthetic Studies on Terpene Compounds. Part 13. Total Synthesis of Fraxinellone". . p. 1557 - 1562. Retrieved 2007/10/02.